Shang Kuan Tsai Chi

July 25, 2011

PattharawadeeThanthranon

What does the word ‘Optimization’ mean?According to Merriam Webster, optimization is a process of making something as effective as possible

With the number of people in the world

increasing, the demands for oil also rise; this

means that oil becomes a lot rarer and a lot

more expensive.

The experiment that is going to be done

during the course of the internship is a reaction

that changes sugar (furfural) into furfural

acetone, a product that can then be further react

to make fuel for cars.

The purpose of the experiment is

to find the base that is the most efficient

in changing sugar to furfural acetone

(C8).

Furfural + Acetone -----> Furfural AcetoneBase

The hypothesis is that NaOH, a strong base, will produce the most furfural acetone when it is allowed to react with the reactants for a long time, because the stronger a base is, the better results it will produce.

1. Lab coat

2. 2-Furaldehyde (0.4145 mL/base)

3. Acetone (0.3676 mL/base)

4. Bases

1. NaOH (0.02 g)

2. KOH (0.028 g)

3. Ca(OH)2 (0.037 g)

4. Mg(OH)2 (0.029 g)

5. Sr(OH)2

6. Ba(OH)2 (0.086 g)

5. Hot plate and stirrer (2)

6. Clamp (4)

7. Stand (2)

8. Bowl (2)

9. Tap water

10. Round-bottom flask 25 mL (2)

11. Gas inlet (2)

12. Cooling Ace (1)

13. Condenser (2)

14. Goggles

15. Magnetic bar (2)

16. Label stickers (6)

17. Micro-pipette (1)

18. Electronic balance (1)

19. Weighing paper (6)

20. Pestle (1)

21. Spatula (2)

22. Joint clip (2)

23. Rubber Tube (1)

24. Tips (12)

25. Gas-Chromatography-Mass

Spectrometer (GCMS)

26. Dropper (4)

27. Syringe (4)

28. Vial (4)

29. Sodium Sulfate

30. Towels (2)

31. BIBASE Rubber support rings (2)

32. Syringe filers (4) (yellow and

pink)

We will be doing 6 reactions (using 6 different bases) in this experiment, but because it will take some time to wait for all of the bases to react one at a time, we

will be doing 2 at once. The following is the procedure…

1. Wrap up the 2 condensers with the towels

2. Set up 2 sets of clamp and stand with 2 clamps

per stand. Make sure the clamp is tightly

clamped

3. Place a hot plate and stirrer beneath the

clamps.

4. Add half bowl of tap water into the bowl.

5. Put the bowl on the hot plate. This is to

prevent a big change in temperature

throughout the day, because water has a high

specific heat.

6. Hold the wrapped up condenser tightly on

the clamp. Make sure the 2 condensers are

hold at the same height and position.

7. Put a gas inlet on the top hole of the

condensers.

8. Hold the 2 tubes from the cooling ace.

9. Plug the tube that pushes water in on the

most bottom hole of one of the

condenser, and the second tube from the

cooling ace on the 2nd most top hole of the

second condenser. This should be done

Gas Inlet

10. Connect the remaining 2 holes on the

condenser with a rubber tube.

11. Set the cooling ace to about 15 degree Celsius

12. Start pumping water from the cooling ace

13. Put a magnetic bar into both round-bottom

flasks. Put a label on the neck of both round-

bottom flasks.

14. Choose 2 bases to work with first (here we will

be doing NaOH and KOH first).

15. Put the 2 bases on weighing paper; one

base per paper.

16. Fold the paper in half so that the bases are

enclose inside

17. Use a pestle to crush the bases into smaller

pieces

18. Measure the amount needed for the 2

bases (as written in the equipment list)

using an electronic balance.

**The next 3 steps should only be done for bases that cone in small grains, not the ones that are powder (Step 17-19)

Pestle

19. Put the bases into the 2 round-bottom flasks;

one bases per flask.

20. Measure 0.4145 mL (to the nearest thousandth)

of 2- furaldehyde using a micropipette.

21. Pour the furfural into one the round-bottom

flasks

22. Change the tip of the micropipette to prevent

any contamination of the next chemical.

23. Measure 0.3676 mL (to the nearest thousandth)

of acetone using the micropipette.

24. Pour the acetone into the same round-bottom

flask

25. Repeat step 22-26 again but this time put the 2-

furaldehyde and acetone into the other round-

bottom flask.

26. Take both round-bottom flasks underneath the

condensers held on the clamps.

27. Use a joint clip to hold both flasks to their

condenser; one clip per flask.

28. Turn on the stirrer to 300 rpm.

29. Wait for the reaction to happen for the next 3

hours.

30. Stop the cooling ace

Hot plate and Stirer

Magnetic Bar Spinning in a Flask

25. Stop the stirrer

26. Remove the joint clips and the round-

bottom flasks

32. Using a dropper, suck out the entire crude

product that is in the flasks into syringes

with yellow filters.

33. Carefully, squeeze the crude product in

the yellow syringes into 2 vials.

Syringe Filter

36. Add Sodium Sulfate into the 2 vials to remove

any water in there. Make sure to add until the

sodium sulfate will slightly move when we

shake the vials.

37. Using new droppers, suck out the liquid

portion from the vials, and squeeze them

into new syringes with pink filters.

38. Carefully, squeeze the liquid into new vials.

39. Close the cap of the vials.

40. Repeat all steps again for 2 more times, but

change the bases to the next 2

Mi shaking the solution

After finishing all the steps, we also did a shorter version of the experiment just to test and

compare the results that we got. This time we did the experiment exactly the same way, but instead

of waiting for 3 hours, we waited only 1.

** After each experiments, don’t forget to wash everything with acetone!

Data 1: 3 hours

Information of the Different BasesBases Observation

of the Base

itself

Pictures Molar

mass

Amount

that is

actually

needed

Amount

that we

put

Solubility (scale

of 1-5, with 5

being the most

soluble)

Observation of the results (color

change, and energy needed to push it

out from the syringe filters)

Gas-Chromatography-Mass Spectrometer

(GCMS)Results

NaOH Small white

grains

(smaller

than KOH)

40 g 0.02 g 0.0251 g 5 The color was still the same as when

we started; odor also stayed the same.

There were formation of

furfural acetone, but

also a lot of C13.

KOH Small white

grains

56.11 g 0.028 g 0.0281 g 5 The color was still the same as when

we started; odor also stayed the same.

Easy to squeeze out from the syringe.

Ca(OH)2 White

powder

74.10 g 0.037 g 0.039 g 1 The product got clearer when

squeezed out of the yellow filter,

because it got separate from the

polymers; there were chunks of

polymers in the flask. Very hard to

squeeze out from the syringe filter.

Left with high amount in

reactants, because they

didn’t react properly and

thoroughly

Mg(OH)2 White

powder

58.33 g 0.0292 g 0.029 g 4 The product got lighter and clearer

when squeezed out of the yellow filter,

because it got separate from the

polymers.

Left with high amount in

reactants, because they

didn’t react properly and

thoroughly

Sr(OH)2 White

powder

121.64 g 0.061 g 4 The product got lighter when

squeezed out of the yellow filter,

because it got separate from the

polymers.

Left with high amount in

reactants, because they

didn’t react properly and

thoroughly

Ba(OH)2 White

powder

171.36 g 0.086 g 3 The product got lighter when

squeezed out of the yellow filter,

because it got separate from the

polymers.

Left with high in

reactants, because they

didn’t react properly and

thoroughly

The peaks at about 8.8 to 9.5 (time) indicate amount

of Furfural Acetone produced

The peaks at about 18.3 (time) indicate amount of C13 produced

The peaks at about 3.5 to 5.5 (time) are the

amount of initial reactants left

unreacted.

Data 2: 1 hour

Information of the Different BasesBases Observation

of the Base

itself

Pictures Molar

mass

Amount

that is

actually

needed

Amount

that we

put

Solubility

(scale of

1-5, with 5

the most

soluble)

Observation of the results (color

change, and energy needed to push it

out from the syringe filters)

Gas-Chromatography-Mass

Spectrometer (GCMS)

Results

NaOH Small white

grains

(smaller

than KOH)

40 g 0.02 g 0.024 g 5 The color was still the same as when

we started; odor also stayed the

same. Easy to push out from the

syringe.

Still has high amount of

unreacted reactants, but also

has a very small amount of

furfural acetone and tinier

amount of C13

KOH Small white

grains

56.11 g 0.028 g 0.0291 g 5 The color was still the same as when

we started; odor also stayed the

same. Easy to push out from the

syringe.

Still has high amount of

unreacted reactants, but also

has a very small amount of

furfural acetone and amount

of C13

Ca(OH)2 White

powder

74.10 g 0.037 g 0.0325 g 2 The product got lighter when

squeezed out of the yellow filter,

because it got separate from the

polymers.

Left with high amount in

reactants, because they didn’t

react properly and thoroughly

Mg(OH)2 White

powder

58.33 g 0.0292 g 0.0271 g 5 The color didn’t change from when

we first started when squeezed out

from the filter.

Left with high amount in

reactants, because they didn’t

react properly and thoroughly

Sr(OH)2 White

powder

121.64 g 0.061 g 0.061 g 4 The product was very hard to squeeze out from the syringe filter, and the ones squeezed out have a

lighter and clearer color.

Left with high amount in reactants, because they didn’t react properly and thoroughly

Ba(OH)2 White

powder

171.36 g 0.086 g 0.0852 g 4 The color did changed to become lighter and clearer when it is

squeezed out from the yellow syringe filter.

Left with high amount in reactants, because they didn’t react properly and thoroughly

-3

The results (graph) show that my hypothesis was correct because stronger bases did indeed produce better results! Secondly, the set of reaction that was done 3 hours also proved that the hypothesis was correct because it got better results than the set that was done in 1 hour. The reasons are because stronger bases make the reaction possible and by waiting for a longer time, we are allowing more furfural and acetone to react, thus producing more furfural acetone. That’s why the reaction was incomplete when we used weaker bases (alkaline earth hydroxides).

However, there was a partial mistake in my hypothesis. This is because when bases get too strong, they might cause further reactions among furfural acetone and the reactants, forming C13. This is why NaOH also produced a large amount of C13 in addition to C8. If we were to do another set of experiment but for 24 hours, there might be some C21 because the products may start to react with each other more often. So in conclusion, KOH should the best base for my experiment, because its basic strength is just right. But as the graph implies, KOH didn’t produce the best results, which means that we must have done something wrong during the process, making the reactants unable to react with each other properly.

There may have been some errors, both human and measurement errors, throughout the experiment, causing slight mistakes in our data and result. Some of the errors might have been inaccurately measured the mass of the base used, not reacting all the bases that were added to the flask, not setting the micropipette to the appropriate value, and not enough sodium sulfate was added. Next time, we would be more careful as so to be more accurate in our results.

Dr.EkasithSomsook

P’AmonwanSayasiri(P’Baitong)

And everyone else in Mahidol